NO309469B1 - Fremstilling av vinylisotiocyanater - Google Patents
Fremstilling av vinylisotiocyanater Download PDFInfo
- Publication number
- NO309469B1 NO309469B1 NO982681A NO982681A NO309469B1 NO 309469 B1 NO309469 B1 NO 309469B1 NO 982681 A NO982681 A NO 982681A NO 982681 A NO982681 A NO 982681A NO 309469 B1 NO309469 B1 NO 309469B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- thiocyanate
- acidic material
- halogen
- isothiocyanate
- Prior art date
Links
- VJCLZQUHGQSTMZ-UHFFFAOYSA-N isothiocyanatoethene Chemical class C=CN=C=S VJCLZQUHGQSTMZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 5
- IFVYHJRLWCUVBB-UHFFFAOYSA-N allyl thiocyanate Chemical class C=CCSC#N IFVYHJRLWCUVBB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 20
- 230000002378 acidificating effect Effects 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000001336 alkenes Chemical class 0.000 claims abstract description 7
- 150000004820 halides Chemical class 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- NYFSGZTZZAYKQO-UHFFFAOYSA-N 3-chloro-1-isothiocyanatoprop-1-ene Chemical group ClCC=CN=C=S NYFSGZTZZAYKQO-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical group ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 claims description 8
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 claims description 8
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkali metal thiocyanate Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 7
- 230000008707 rearrangement Effects 0.000 description 7
- KLFSZAVVJVHPTD-OWOJBTEDSA-N [(e)-3-chloroprop-2-enyl] thiocyanate Chemical compound Cl\C=C\CSC#N KLFSZAVVJVHPTD-OWOJBTEDSA-N 0.000 description 5
- 150000002540 isothiocyanates Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- VCAWEGCDGOALHI-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole;hydrochloride Chemical compound Cl.ClCC1=CN=C(Cl)S1 VCAWEGCDGOALHI-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/04—Substitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9712409.3A GB9712409D0 (en) | 1997-06-14 | 1997-06-14 | Preparation of vinyl isothiocyanates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO982681D0 NO982681D0 (no) | 1998-06-11 |
| NO982681L NO982681L (no) | 1998-12-15 |
| NO309469B1 true NO309469B1 (no) | 2001-02-05 |
Family
ID=10814165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO982681A NO309469B1 (no) | 1997-06-14 | 1998-06-11 | Fremstilling av vinylisotiocyanater |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6069255A (sk) |
| EP (1) | EP0885882A1 (sk) |
| JP (1) | JPH1149745A (sk) |
| KR (1) | KR19990006904A (sk) |
| CA (1) | CA2240422A1 (sk) |
| FI (1) | FI981251A (sk) |
| GB (2) | GB9712409D0 (sk) |
| HU (1) | HUP9801344A3 (sk) |
| IN (1) | IN184313B (sk) |
| NO (1) | NO309469B1 (sk) |
| TW (1) | TW410222B (sk) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5180833A (en) * | 1990-03-16 | 1993-01-19 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
| GB2305172B (en) * | 1995-09-14 | 1998-11-18 | Fine Organics Ltd | Preparation of substituted thiazoles |
| IN182219B (sk) * | 1996-02-21 | 1999-02-06 | Kuraray Co |
-
1997
- 1997-06-14 GB GBGB9712409.3A patent/GB9712409D0/en active Pending
-
1998
- 1998-06-01 IN IN973CA1998 patent/IN184313B/en unknown
- 1998-06-01 EP EP98304301A patent/EP0885882A1/en not_active Withdrawn
- 1998-06-02 GB GB9811807A patent/GB2326162B/en not_active Expired - Fee Related
- 1998-06-02 FI FI981251A patent/FI981251A/fi unknown
- 1998-06-02 US US09/088,836 patent/US6069255A/en not_active Expired - Fee Related
- 1998-06-11 NO NO982681A patent/NO309469B1/no not_active IP Right Cessation
- 1998-06-12 CA CA002240422A patent/CA2240422A1/en not_active Abandoned
- 1998-06-12 HU HU9801344A patent/HUP9801344A3/hu unknown
- 1998-06-12 KR KR1019980021839A patent/KR19990006904A/ko not_active Application Discontinuation
- 1998-06-15 JP JP10166860A patent/JPH1149745A/ja active Pending
- 1998-07-09 TW TW087111130A patent/TW410222B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU9801344D0 (en) | 1998-08-28 |
| EP0885882A1 (en) | 1998-12-23 |
| HUP9801344A2 (hu) | 1999-03-29 |
| TW410222B (en) | 2000-11-01 |
| GB9712409D0 (en) | 1997-08-13 |
| NO982681D0 (no) | 1998-06-11 |
| FI981251A (fi) | 1998-12-15 |
| CA2240422A1 (en) | 1998-12-14 |
| GB2326162B (en) | 2001-02-07 |
| GB2326162A (en) | 1998-12-16 |
| IN184313B (sk) | 2000-08-05 |
| US6069255A (en) | 2000-05-30 |
| GB9811807D0 (en) | 1998-07-29 |
| HUP9801344A3 (en) | 1999-04-28 |
| KR19990006904A (ko) | 1999-01-25 |
| JPH1149745A (ja) | 1999-02-23 |
| NO982681L (no) | 1998-12-15 |
| FI981251A0 (fi) | 1998-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN DECEMBER 2001 |